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E4143

(−)-Epigallokatechingallat

≥95%

Synonym(e):

(−)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallat, (−)-cis-3,3′,4′,5,5′,7-Hexahydroxy-Flavan-3-Gallat, EGCG

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Ihnen/SKUVerfügbarkeitPreis
50 mg
Warenkorb auf Verfügbarkeit prüfen
€ 214,00

Über diesen Artikel

Empirische Formel (Hill-System):
C22H18O11
CAS-Nummer:
Molekulargewicht:
458.37
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352205
MDL number:

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Quality Segment

assay

≥95%

solubility

H2O: ≥5 mg/mL, clear

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c4cc(O)c(O)c(O)c4

InChI

1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1

InChI key

WMBWREPUVVBILR-WIYYLYMNSA-N

Gene Information

human ... CYP1A2(1544)

General description

(−)-Epigallocatechingallat aus grünem Tee ist der bioaktive Hauptbestandteil, der 50–80 % des gesamten Catechingehalts ausmacht.[1] Seine chemische Struktur ähnelt der von Epicatechingallat (ECG), einem Ester der Gallussäure und Epigallocatechin.[2]

Application

(-)-Epigallokatechingallat wird verwendet:
  • als Anti-Tumor-Wirkstoff für die metastatische TRAMP-Prostatazelllinie von Mäusen mittels Zellproliferations-Assay, Apoptosedetektion und modifiziertem Boyden-Kammer-Assay
  • zur Induktion von Zelltod in akuter myeloischer Leukämie durch einen Zelltod-assoziierten Proteinkinase-2-Weg, der mittels Zelllebensfähigkeit, Zellzyklus und Apoptose-Assay analysiert werden kann
  • als Hemmer der Osteoklastendifferenzierung der Preosteoklasten-Zelllinie RAW264.7 der Maus
  • zur Förderung der myogenen Differenzierung

Biochem/physiol Actions

(-)-Epigallokatechingallat (EGCG), ein antioxidatives Polyphenol-Flavonoid, weist Anti-Tumor-Eigenschaften auf, indem es die Telomerase- und DNA-Methyltransferase-Aktivität hemmt.[1] EGCG hemmt die Expression von Matrix-Metalloproteinase-2 (MMP-2), MMP-9 und reduziert die Invasivität. EGCG blockiert die Aktivierung der epidermalen Wachstumsfaktor(EGF)-Rezeptoren und des menschlichen epidermalen Wachstumsfaktor-Rezeptors-2 (HER-2).[1] EGCG erhöht die Knochenmineraldichte und reduziert die Knochenresorption. EGCG hemmt die Osteoklastogenese durch Hemmung des Rezeptoraktivators der von Kernfaktor-κ-B-Liganden (RANKL) induzierten Kernfaktor-κ-B-(NF-κB-)Transkriptionsaktivität. EGCG reduziert Skelettmuskelatrophie. EGCG hat Anti-Aging-Eigenschaften und erhöht die Myogendifferenzierung. EGCG hemmt Fettsäure-Synthase- und Glutamat-Dehydrogenase-Aktivität.

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Dieser Artikel
E4268PHR1333324880
assay

≥95%

assay

≥80% (HPLC)

assay

-

assay

≥95% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

pharmaceutical (small molecule)

application(s)

-

Quality Level

200

Quality Level

200

Quality Level

300

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

solubility

H2O: ≥5 mg/mL, clear

solubility

-

solubility

-

solubility

water: 5 mg/mL, DMSO: soluble

Gene Information

human ... CYP1A2(1544)

Gene Information

human ... CYP1A2(1544)

Gene Information

-

Gene Information

-


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pictograms

Exclamation markEnvironment

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1

Lagerklasse

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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Questions

1–9 of 9 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  3. What is the solution stability of (-)-Epigallocatechin gallate (E4143)?

    1 answer
    1. A solution of (-)-Epigallocatechin gallate in water at a concentration of 0.3 mg/mL was found to have significantly decreased in purity (from 99.6% to 81.7%) after 2.5 hours at room temperature. A similar solution of (-)-Epigallocatechin gallate in water at a concentration of 0.3 mg/mL was found to have decreased in purity only slightly (from 99.5% to 99.3%) after 2.0 hours at 4°C.

      Helpful?

  4. Is (-)-Epigallocatechin gallate (Product No. E4143) for human use

    1 answer
    1. No. Product No. E4143 ((-)-Epigallocatechin gallate) is for laboratory research use only, not for human use.

      Helpful?

  5. How does the storage temperature relate to shipping conditions?

    1 answer
    1. The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment.

      Helpful?

  6. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

      Helpful?

  7. Is (-)-Epigallocatechin gallate (Product No. E4143) sterile and tested for endotoxins?

    1 answer
    1. Product No. E4143 ((-)-Epigallocatechin gallate) is not prepared under sterile conditions and has not been tested for endotoxins.

      Helpful?

  8. Can (-)-Epigallocatechin gallate be determined in plasma and urine?

    1 answer
    1. The determination of (-)-Epigallocatechin gallate in plasma and urine by HPLC has been reported in Cancer Epidemiol. Biomark. Prev., 4, 393 (1995).

      Helpful?

  9. What is the solubility of (-)-Epigallocatechin gallate (E4143)?

    1 answer
    1. We have tested the solubility of (-)-Epigallocatechin gallate at 5 mg/mL in water.

      Helpful?

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